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Stef and the City

Chicago Matchmaking Services

  • Dating these days is HARD. It’s hard to know where the BEST places are to meet someone.
  • Has it been months since you’ve last had a GOOD date?
  • Do you need a new selection of people to meet?
  • Are you finding that you don’t know the rules of how dating works these days?
  • Has it gotten a lot harder to meet people since you graduated college and since your friends have
    gotten married? 
  • Do you find that your social life needs a boost? 

Chicago matchmaker Stef, at Stef and the City is an alternative to costly introduction services that might not have
the types of people you are looking for. We have the BEST prices among Chicago dating services, and offer the BEST options for singles. It’s personalized matchmaking! Not only do we have a great database of people, but we also continually search for new clients that fit what our clients are looking for. We continue to bring new people into our service on a daily basis, and offer many types of dating services for professionals! Whether it’s having our staff go out and about, our constant publicity, or world of mouth- we get that NEW people need to come in to make our service successful. We believe in honesty about what we can provide for you and the timeline that it takes to do so. We would rather wait or search for you than to give you the wrong matches.

Gentleman, we know you are looking for a two-way street in dating. Meet local single women who are also invested emotionally and financially. Meeting single women has never been so easy!

Our introduction service stays true to what people need- your own personal recruiter! Fill out our questionnaire today! 
It’s no obligation if you fill out a questionnaire, and remember you only have things to gain by contacting us. If we don’t have a match for you today, you never know who we might meet for you tomorrow. You can find an initial questionnaire on our CONTACT US page.

Keep in mind we are MORE than just an introduction service. Be sure to check out all we have to offer under the Services tab at the top of this page. Not only do we handle making introductions, but we have:

  • Dating coaching: New into dating after a long time? Gone through a recent divorce? Unsure why you are not getting the results you want? Get your own dating advisor.
  • Personalized social calendars: Maximize your time by getting assistance with personal life planning. Be where you need to be to meet the people that fit YOUR needs for relationships and friendships.
  • Events: We know where to go! As seen on ABC7, CBS2, NBC5, WCIU’s “You and Me This Morning” and more we tell about the places to be at along with special Stef and the City discounts!
  • Singles travel: Do you need to find places to travel that you are not the only single person? Do you want to travel internationally or abroad? We have the BEST prices and know the 411 on what you need to know!

We cater to MANY ages groups: whether you are in your 20’s, 30’s, 40’s or 50’s- we have the people you want to meet! Check out our Casting Call  page- we have new singles listed monthly. We may already have your match!



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